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Great Day in Sales

Great Day in Sales
Author: Justin Ashby
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© 2025 Great Day in Sales
Description
Sponsored by Alysio
We've gathered the best sales leaders across the United States, Canada and UK to answer the question "What does a great day in sales look like?"
You can't close a 6 or 7 figure deal every day. So what are you doing to make sure you take advantage of every minute?
We'll explore frameworks, scorecards, and philosophies of the best sales people at leading sales lead companies.
Join us to learn more on your journey from SDR, BDR or AE to becoming the sales leader you aim to be.
54 Episodes
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Summary In this episode, Nikki Lang emphasizes the importance of maintaining a human connection in sales. Nikki shares her journey into tech sales, highlighting her experiences and the significance of soft skills in building relationships with buyers. She discusses the need for warmth and empathy in sales interactions, the balance between rapport building and discovery, and the importance of self-connection for genuine engagement. The conversation concludes with Nikki's perspective on what co...
Summary Colin Specter, SVP at Orum, shares his journey from being the original sales hire to scaling the sales team at Orum. Colin discusses the importance of technology in sales, the challenges of building a sales team, and his strategies for training and enabling new hires. He emphasizes the need for documentation, feedback loops, and the significance of maintaining a positive mindset for success in sales.TakeawaysThe importance of technology in sales, particularly AI solutions, can signifi...
Summary Helen Calvin, the new CEO of Buildout, shares her unique journey from a background in behavioral psychology to becoming a sales leader and eventually a CEO. The conversation explores the importance of understanding customer psychology in sales, the transition from CRO to CEO, and the need for a shift in compensation structures to motivate sales teams effectively. Helen emphasizes the significance of celebrating small wins and maintaining a customer-centric approach in all roles ...
In this episode of the Great Day in Sales podcast, Justin interviews Ron Halbert, Vice President of Sales Development at Sirion. Ron shares his extensive background in software sales and discusses the importance of understanding the ideal customer profile (ICP) for contract management. He emphasizes the challenges faced by sales development representatives (SDRs) when engaging with high-level executives and the critical factors contributing to scalable SDR organizations' success. Ron also hig...
SummaryMike Rhea, the Chief Revenue Officer at Intelligent Technical Solutions discusses his extensive background in sales, his journey through various companies and the strategies he employs to scale sales teams effectively. He emphasizes the critical role of discovery in the sales process, explaining how understanding a prospect's problems can lead to successful outcomes. Mike also delves into the importance of pricing and value perception, as well as the significant impact of leadership on...
SummaryEllen Rataj, former member of the sales force at HubSpot, shares insights on scaling sales teams and implementing change management. She emphasizes the importance of positive thinking, effective communication, and cross-functional alignment. Ellen highlights the power of small wins and recognizing the good in each day as a measure of success in sales. In this episode, Ellen dives into the challenges of navigating organizational change and the strategies that have proven effective in ...
SummaryMeredith Chandler, Head of New Business at Unicrn, discusses her career in sales and the rise of fractional sales leadership. She shares her experiences working at companies like Yelp, Indeed, Samsara, SPIF, and Captivate IQ. Meredith explains the concept of fractional sales and how it can benefit companies looking to scale their sales teams without the cost of hiring full-time employees. She also emphasizes the importance of coaching and continuous learning in sales. A great day in sa...
SummaryMichael Cupps, Executive Vice President of Growth at Active Ops, discusses the behaviors and habits of successful sales teams. He emphasizes the importance of managing time effectively and prioritizing tasks based on values and goals. Cupps shares strategies for stacking activities and using technology to improve productivity. He also highlights the need for sales reps to reflect on their actions and make adjustments as necessary. A great day in sales, according to Cupps, involves prog...
SummarySam Nelson, founder of strleader.com and creator of the Pipeline Pipeline conference, shares his journey from selling funeral insurance to becoming an expert in SDR training and consulting. He emphasizes the importance of simplifying operations in SDR organizations and focusing on repeatable processes. Sam discusses the unique challenges and opportunities in enterprise sales and highlights the value of building a community of SDR leaders. He also shares his excitement for, and invites ...
SummaryAnthony Delonardo, VP of Sales at LinenMaster, joins Justin Ashby on the Great Day in Sales podcast. They discuss the importance of mindset in sales and how focusing on controllables and daily execution can lead to success. They also talk about the challenges of selling in a niche industry and the need to create a sense of urgency for potential customers. Anthony emphasizes the value of agency in sales and the importance of educating customers based on the salesperson's institutional k...
SummaryBrooke Searle, an SDR manager at Podium, shares her unconventional path into sales and her experience leading an SDR team. She discusses the importance of building belief in her team members and helping them achieve their goals. Brooke emphasizes the value of understanding the personal lives and aspirations of her team members and how it contributes to their success. She also highlights the continuous learning and development opportunities in the sales industry.TakeawaysBuilding belief...
SummaryTyler Denboer, VP of Sales at Office Ally, shares his career path and experiences in sales leadership. He emphasizes the importance of having the right people on the team and providing them with proper coaching and enablement. Tyler discusses the challenges of building out the sales and marketing organization at Office Ally and the need for strong frameworks and processes. He also talks about the metrics that matter and the significance of executing against them every day. Tyler believ...
Adam Robinson, CEO and co-founder of Retention.com and RB2B, discusses his journey as an entrepreneur and the success he has achieved in hitting the million ARR milestone with each startup. He shares his insights on the power of building an audience on LinkedIn and the challenges of implementing a product-led growth (PLG) strategy. Adam also explores the concept of being transparent and controversial in his content, the importance of offering a free product, and the potential for lower churn ...
SummaryRyan Jump, the director of sales at Scorpion, shares insights on managing a sales team, focusing on the individual, and the transition to selling to home service companies. He emphasizes the importance of understanding and addressing the unique needs of each sales rep and the value of building trust and authenticity within the team. Ryan also discusses the concept of designing your day and the significance of intentional and disciplined daily actions in sales.TakeawaysUnderstanding the...
SummaryJason Jordan, author of 'Cracking the Sales Management Code,' discusses the importance of focusing on the right opportunities and optimizing the sales pipeline. He emphasizes the need for sales leaders to coach their teams and highlights the value of consultative selling in certain industries. Jordan also shares insights on the different sales roles and the importance of aligning the sales process with the buyer's needs. A great day in sales, according to Jordan, involves productivity,...
SummaryLeslie Venetz, founder of a sales-led go-to-market agency, shares her journey in sales and content creation. She highlights the importance of community, knowledge sharing, and tailoring content for different platforms like LinkedIn and TikTok. Leslie discusses her sales methodology, focusing on earning the buyer's attention, and offers resources like objection scripts and voicemail tips. She emphasizes personalized outreach, data-driven decision-making, and balancing metrics. Leslie al...
SummaryIn this podcast episode, Justin interviews Alex Knight, the CRO of Snoball. They discuss Alex's background, the evolution of Snoball from a business listing site to a SaaS product, and the indicators that led to the decision to focus on software. They also talk about the maturity level of companies when it comes to referrals and the skills that have benefited Alex in his role as CRO. They touch on hiring strategies, time management as a sales leader, and the future goals of Snoball.Tak...
SummaryVin Matano, a sales professional and content creator, shares his insights on personal branding and the benefits of creating content on LinkedIn. He emphasizes the importance of employees building their personal brands and how it can positively impact the company they work for. Vin also discusses his career at Demandbase and the value of staying with a company for an extended period of time. He shares his perspective on what a great day in sales looks like, which includes prospecting, c...
SummaryMelissa Gaglione shares her unique career path and how she transitioned from being a teacher to a news reporter to a successful sales professional. She discovered the power of video selling during her time as an SDR and used it to book meetings with C-suite executives from Fortune 500 companies. Melissa emphasizes the importance of not riding the roller coaster of sales and focuses on maintaining a balanced approach. She also discusses how she coaches others on video selling and the va...
SummaryBrooke Goddard, a sales leader at Design Pickle, discusses the unique challenges and strategies of selling to creatives. She shares her background in sales and highlights the importance of creativity in the sales process. Brooke emphasizes the need to stand out and be creative when reaching out to potential customers, including using motion graphics and personalized videos. She also emphasizes the importance of a strong sales and marketing partnership and the value of radical candor an...
SummaryKody Klenow, Vice President of Local Revenue at Lee Enterprises, shares insights into sales leadership and managing a large sales team across multiple markets. He discusses his career path and the unique sales program he graduated from. Kody emphasizes the importance of being a connector across the organization and fostering collaboration among sales teams in different markets. He also highlights the significance of hiring salespeople who are involved in and knowledgeable about the loc...
SummaryKevin Dorsey shares his insights on leadership and building successful sales teams. He emphasizes the importance of defining what good looks like and following the four D's: define, document, demonstrate, and deliberately practice. Kevin also highlights the value of customer interviews in understanding the buyer's perspective and tailoring messaging. He encourages salespeople to focus on making prospects want the product rather than just understanding it. A great day in sales, accordin...
SummaryTaylor Safford, CRO at Netcraft, shares his journey from being one of the earliest hires at Qualtrics to leading sales teams and scaling offices. He emphasizes the importance of embracing a mindset shift and focusing on leading indicators to achieve success in sales. Taylor discusses the challenges and lessons learned from scaling sales teams and highlights the significance of defined roles, expectations, and accountability in building successful relationships. He also explains the con...
SummaryIn an exclusive conversation, George, the Chief Revenue Officer at Recharge, unveils the secrets to crafting a thriving sales career and ascending to the ranks of a true sales virtuoso. With fervor and finesse, he imparts the wisdom of transcending the mere title of a salesperson, advocating for the transformation into a consummate sales professional. Through the prism of his own journey, George underscores the pivotal role of harmonizing success and fulfillment, fashioning a cult...
SummaryBuckle up for a dynamic ride as Justin sits down with Kevin Mulrane, the VP of Sales powerhouse at BioSentry. In this electrifying episode, Kevin spills the beans on his thrilling journey in sales leadership and the art of crafting sales playbooks that pack a punch. Get ready to be energized as Kevin dishes out his top-notch insights on seamlessly integrating into seasoned teams, turbocharging team performance through coaching, and mastering the art of time management as a sales leader...
SummaryLuke Wilson, CEO of Signpost, shares his journey to his current role and his passion for serving small to medium businesses. He discusses the challenges and opportunities of stepping into a remote organization as CEO and emphasizes the importance of building a strong go-to-market motion. Wilson highlights the value of investing in training and development for sales teams and the need to focus on upselling and cross-selling to existing customers. He concludes by emphasizing the importan...
Morgan Ingram, everyone! Huge following on LinkedIn, incredible advisor to many brands, and has his own company to consult and help built incredible sales orgs. In this conversation, Morgan and Justin discuss what makes a great day in sales, setting goals, and productivity levers. They emphasize the importance of reverse engineering goals and aligning activities with those goals. They also discuss the significance of personal and professional goals and how they drive motivation...
SummaryScott Lease has been part of 11 exits, and worked with 12 unicorns. He's got one of the most storied backgrounds in Silicon Valley and has since made the move to Austin to continue building and scaling sales organizations. In this episode, he emphasizes the importance of putting sales processes on paper and customizing solutions for each company. So many people run their sales orgs from their heads - it doesnt work! Scott also highlights the significance of tracking leading indicators...
SummaryJustin Ashby interviews Jeff Torbeck, VP of Revenue at Gun.io. They discuss various topics related to sales management and team building and focus in on how a high performing team can be a place of constant learning. Jeff shares his insights on focusing on individual performance, balancing quota performance and team fit, and the evolving perception of sales as a valued profession.d The conversation emphasizes the importance of collaboration, continuous learning, and customer-centric se...
SummaryJoin a riveting conversation with Donald Kelly as he unravels the art of mastering LinkedIn for prospecting and sales. In this dynamic discussion, Donald unveils the secrets to regularly connecting with key individuals, delivering valuable content, and sparking engagement. Brace yourself for insights into injecting personality into your LinkedIn presence and leveraging your company page to forge connections. Donald and Justin unveil the Connect, Share, Engage method, empowering sales p...
SummaryEmbark on a captivating journey with Justin as he sits down with Alyson Baber, a brilliant VP of Sales at Outreach.io. Allyson's unconventional career trajectory is not uncommon, but very fascinating. From chemical engineering to medical sales, she's now leading one of the most dynamic teams of sales people in tech. Allyson shares her invaluable strategies for building trust and managing expectations within her team. She reflects on her experiences in high-growth companies, p...
SummaryEmbark on an exhilarating journey with Justin as he ventures into the realm of sales mastery alongside the esteemed Mike Wolber, the ingenious Chief Revenue Officer of Rent Dynamics. Mike unveils the blueprint for crafting a thriving sales organization. Prepare to be captivated as Mike shares his visionary approach to recruitment, advocating for the hiring of sales academics and the formulation of a robust go-to-market strategy. Brace yourself for a whirlwind of insights as Mike ...
Justin and Jen discuss various aspects of sales, including selling like a buyer, the importance of likability, applying a buyer-centric approach, understanding trade-offs, insights from sales kick-offs, promoting organic content sharing, building sales teams, the role of subject matter experts, and creating a great day in sales. They emphasize the need to understand the buyer's perspective and tailor the sales approach accordingly. They also highlight the value of building relationships and p...
SummaryDelve into the fascinating world of sales with Kyle Asay, the visionary VP at MongoDB, as he unveils the secrets behind his remarkable career journey and the evolution of his groundbreaking sales frameworks. With a blend of wisdom and innovation, Kyle emphasizes the transformative power of personal development and the art of tailoring sales processes to individual strengths. From dissecting team structures to navigating the complexities of remote work, Kyle offers unparalleled insights...
SummaryIn this riveting episode, Justin Ashby delves into the world of sales development with none other than Gabe Lullo, the mastermind CEO behind Alley-oop, an SDR agency. With passion and expertise, they navigate through the intricate landscape of sales, tackling crucial topics such as the art of onboarding SDRs, the enduring significance of phone calls in outbound sales, and the untapped potential of LinkedIn as a sales powerhouse. Venturing further, they explore the transformative shift ...
SummaryEmbark on an exhilarating journey with Justin as he unravels the fascinating career narrative of Collin Mitchell, the dynamic managing partner at Leadium, a fractional SDR agency. Join them in exploring the evolution from Collin's early days in sales to the creation and sale of multiple companies. Discover the untold benefits of partnering with a fractional SDR agency and delve into the pivotal role of a quality-centric approach in outbound sales. Collin sheds light on the art of perso...
SummaryIn this episode, join Justin in an exhilarating interview with Ryan Milligan, the VP of Sales at QuotaPath, as they unravel the captivating story behind Ryan's ascent to sales leadership. Delve into the intricacies of aligning compensation plans with corporate goals and crafting dynamic structures. Uncover the art of open conversations with sales reps and the secrets to motivating them effectively. Brace yourself for a thought-provoking discussion on incentivizing marketing teams, wher...
SummaryMary Kheedo, Vice President of Sales at Growth Loop, shares her insights on the first 30 days in a new sales leadership role. She discusses her background in sales, including her experience at HubSpot and Lytics. Mary emphasizes the importance of creating a 30, 60, 90 day plan and building trust with the team. She also highlights the need for relentless prioritization and the value of self-reported quick wins. Overall, Mary provides valuable advice for sales leaders transitioning into ...
SummaryStep into the World of Sales Excellence with Justin Otley, Head of Talk Desk's Dynamic Sales Development Team! Uncover the Secrets Behind Career Milestones, A Players' Magic, and the Art of Crafting Your Best Day in Sales. Elevate your strategy as Justin spills the beans on promoting from within, unleashing A Players, and turning team motivation into a powerhouse of success!TakeawaysPromoting from within is crucial for building a successful sales development team.A players are essentia...
SummaryIn this podcast episode, Katie Ward shares her journey in tech sales and her role in building up the next generation of women leaders. She emphasizes the importance of physical health in sales and how it contributes to overall performance. Katie also discusses the unique challenges women face in the workplace and how she helps them overcome imposter syndrome. She introduces the RAP framework for sales, which stands for Reflect, Assess, and Plan, and explains how it helps her stay organ...
SummaryDevin Williams, from Instabug, discusses the importance of emotional intelligence (EQ) in sales and how it can lead to success. He shares his career background and highlights from the biggest deal in Instabug history. Devin explains that EQ is the key to understanding oneself and others, and it can improve various skills such as active listening, empathy, and relationship building. He provides frameworks and practices for developing EQ and emphasizes the importance of leading by exampl...
SummaryIn this episode of the Great Day in Sales podcast, Justin interviews Matt Buchalski, the VP of Sales at RealPage. Matt shares his background and career journey, which includes transitioning from financial sales to technology sales. He discusses the changes and growth he has experienced at RealPage, including the company's acquisition and the impact of COVID-19 on the housing market. Matt emphasizes the importance of team building and promoting from within, highlighting the value of tra...
SummaryIn this podcast episode, Tony Bennett shares her journey from sales at UPS to becoming a VP of Sales at Daily. She discusses her experience of building sales from zero to 20 million at Terminus and the importance of problem-solving in sales. Tony emphasizes the need to focus on value and avoid perfectionism when enabling others to sell. She also highlights the different selling stages and the importance of adapting to change. Tony shares principles for sales leaders, including the impo...
SummaryGreg Costigan, a sales expert with experience in Silicon Valley, shares valuable insights on sales strategies and success. He introduces the Give, Get, Goal framework, emphasizing the importance of preparation and differentiation in sales calls. Greg also highlights the significance of building rapport and establishing hunger in sales interactions. He discusses the value of individualized communication and warm referrals in outbound sales. Finally, Greg shares that great days in sales ...
SummaryChet Lovegren, also known as the Sales Doctor, discusses his methodology for sales training and enablement. He emphasizes the importance of understanding the specific needs and challenges of each sales team and provides a tailored prescription for success. We discuss the resurgence of cold calling and the need for a balanced approach to outbound sales. He highlights the significance of participation and engagement in sales teams and the role of coaching in developing top performer...
SummaryAmir Torabi, VP of Sales at Sendlane, shares his journey from a sales role in a recruitment agency to his current position. He emphasizes the importance of identifying one's strengths and being open to new opportunities. Amir discusses the market shifts that led to Sendlane's growth and the strategies they implemented to adapt. We highlight the significance of deal inspection and the need to focus on high-potential leads. Something that many companies fail to do anything with.&nbs...
Join us as we chat with Jessica, the VP of Sales at Deskera. Jessica walks us through her sales journey and her leap from a large organization to a startup. You'll gain insights into how she hones her problem-solving skills to tackle different areas of the business and the importance of segmentation in propelling the business forward and pinpointing the ideal customer. This riveting discussion underscores the perks of concentrating on segmentation for both team and company growth.We'll also u...
Join us as we interview Kyle Poll, a seasoned sales leader, as he narrates his intriguing career path including Linkedin and Gympass in the US. Kyle shares how a variety of roles, including missionary work and his experience in financial services, helped shape his understanding of sales. He vividly details his nine-year tenure at LinkedIn during its early days and how he helped shape its growth. Kyle provides fascinating insights into his transition from LinkedIn to Gympass. He details h...
Imagine navigating the intricate labyrinth of PropTech sales, moving your company from high-velocity small business sales to a more enterprise-focussed approach. That’s exactly what our guest, John, has done over his 15-year sales career, including stints at industry giants like Cisco. In this illuminating conversation, we explore the unique facets of PropTech, a realm distinct from other industries, and the opportunities ripe for the taking. Hear about John’s transition journey with Valkyrie...
We are joined by Dustin Sears, a seasoned sales expert at Intellishift, who shares the secrets behind his team's incredible tripling of production within just a year. Listen in as he explains the importance of creating an environment that not only fosters a strong work ethic but also encourages fun and camaraderie. Dustin gives us a peek into the workings of IntelliShift, an all-in-one fleet platform that has revolutionized fleet management with integrated GPS telematics, AI dash cameras...
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